Quinoline derivative efficient catalytic synthesis method

A technology for quinolines and derivatives, which is applied in the field of efficient catalytic synthesis of quinoline derivatives, can solve the problems of low utilization rate of reaction raw materials, difficult biodegradation of catalysts, complicated operation processes, etc., and achieves easy industrialized large-scale production, The effect of many cycles and simple synthesis process

Active Publication Date: 2015-01-28
南京苏亦欣医药科技有限公司
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  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

[0005] The purpose of the present invention is to overcome the disadvantages of complex operation process, low utilization rate of reaction raw materials, difficult biodegradation and serious loss of catalyst in the process of catalytic synthesis of quinoline derivatives by using acidic ionic liquid in the prior art, and provide a Easy biodegradation, higher acidity, simple preparation, and low-cost polysulfonate acidic ionic liquid are used as green catalysts, and 75% ethanol aqueous solution is used as a method for catalytically synthesizing quinoline derivatives under the condition of solvent

Method used

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  • Quinoline derivative efficient catalytic synthesis method
  • Quinoline derivative efficient catalytic synthesis method
  • Quinoline derivative efficient catalytic synthesis method

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0024] Add 10mmol 2-aminoacetophenone, 10mmol ethyl acetoacetate, 0.8mmol polysulfonate acidic ionic liquid catalyst and 30ml 75% ethanol aqueous solution into a 100ml single-necked bottle equipped with a condenser. The reaction was heated to reflux, and the progress of the reaction was tracked by thin-plate chromatography (TLC) (developing solvent: ethyl acetate:petroleum ether=1:4). The reaction took 7 minutes. After the reaction was completed, it was cooled to room temperature, filtered, and the resulting filter residue was vacuum-dried to obtain pure ethyl 2,4-dimethylquinoline-3-carboxylate with a yield of 92%. The filtrate was directly added with 2-aminoacetophenone and ethyl acetoacetate for repeated use.

[0025] 2,4-Dimethylquinoline-3-carboxylic acid ethyl ester: 1 H NMR (300MHz, CDCl 3 ): δ=1.62(t, J=7.0Hz, 3H), 2.97(s, 3H), 3.08(s, 3H), 4.69(q, J=7.0Hz, 2H), 7.72~8.33(m, 4H)

Embodiment 2

[0027] Add 10mmol 2-aminoacetophenone, 10mmol cyclopentanone, 0.8mmol polysulfonate acidic ionic liquid catalyst and 30ml 75% ethanol aqueous solution into a 100ml single-necked bottle equipped with a condenser. The reaction was heated to reflux, and the progress of the reaction was tracked by thin-plate chromatography (TLC) (developing solvent: ethyl acetate:petroleum ether=1:4). The reaction time was 6 minutes. After the reaction was completed, it was cooled to room temperature, filtered, and the resulting filter residue was vacuum-dried to obtain pure 9-methyl-2,3-dihydro-1H-cyclopenta[b]quinoline with a yield of 93%. Directly add 2-aminoacetophenone and cyclopentanone to the filtrate for repeated use.

[0028] 9-methyl-2,3-dihydro-1H-cyclopenta[b]quinoline: 1 H NMR (300MHz, CDCl 3 ): δ=2.05(m, 2H), 2.41(s, 3H), 2.88(s, J=7.5Hz, 2H), 3.23(t, J=7.0Hz, 2H), 7.39~7.94(m, 4H)

Embodiment 3

[0030] Add 10mmol 2-aminoacetophenone, 10mmol cyclohexanone, 0.7mmol polysulfonate acidic ionic liquid catalyst and 40ml 75% ethanol aqueous solution into a 100ml single-necked bottle equipped with a condenser. The reaction was heated to reflux, and the progress of the reaction was tracked by thin-plate chromatography (TLC) (developing solvent: ethyl acetate:petroleum ether=1:4). The reaction took 9 minutes. After the reaction was completed, it was cooled to room temperature, filtered, and the resulting filter residue was vacuum-dried to obtain pure 9-methyl-1,2,3,4-tetrahydroacridine with a yield of 95%. Directly add 2-aminoacetophenone and cyclohexanone to the filtrate for repeated use.

[0031] 9-methyl-1,2,3,4-tetrahydroacridine: 1 H NMR (300MHz, CDCl 3): δ=1.69(m, 4H), 2.21(s, 3H), 2.58(t, J=7.6Hz, 2H), 2.89(t, J=7.6Hz, 2H), 7.17~7.80(m, 4H)

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Abstract

The invention discloses a quinoline derivative efficient catalytic synthesis method belonging to the technical field of organic synthesis. The molar ratio of an active alpha-methyl or methylene carbonyl compound and 2-amino acetophenone is 1: 1, the molar amount of a multi sulfonic acid r adical acidic ionic liquid catalyst is 7-10% of the use amount of the 2-amino acetophenone, the reaction solvent 75% ethanol aqueous solution volume (ml) is 3-5 times of the molar amount (mmol) of the 2-amino acetophenone, the reflux reaction time is 5-25min, a filter residue is obtained by cooling to room temperature after the reaction and filtering, and the obtained filter residue is dried under vacuum to obtain a pure quinoline derivative. Compared with a synthesis method using other acidic ionic liquid as a catalyst, the catalyst has high catalytic activity, less use amount and less loss quantity during the circulation use, and the whole synthetic process has the advantages of being simple, convenient, economic and the like, and is convenient for industrialized mass production.

Description

technical field [0001] The invention belongs to the technical field of organic synthesis, and in particular relates to a method for efficiently catalytically synthesizing quinoline derivatives. Background technique [0002] Many quinoline derivatives are widely used in medicine, molecular biology, luminescent materials, dyes, food and feed additives, pesticides and other fields due to their special biological and physiological activities, as well as electron-rich aromatic systems. The methods for synthesizing quinoline derivatives mainly include Skraup method, Combes method, Friedlaender method, Pfitzinger method and Doebner-von Miller method. Among them, the Friedlaender method is one of the most important and direct methods for the synthesis of quinoline derivatives. Its basic form is the condensation reaction of o-amino aromatic carbonyl compounds with active α-methyl or methylene carbonyl compounds. This method traditionally uses protons or Lewis acids as catalysts, but...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D215/54C07D215/04C07D221/16C07D219/02
CPCC07D215/04C07D215/54C07D219/02C07D221/16
Inventor 岳彩波查荣轩吴胜华叶晨廖凯粱莹储昭莲
Owner 南京苏亦欣医药科技有限公司
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